Syntheses And Properties Of Novel Triazine-BODIPY Derivatives

BODIPY fluorescent dye is a class of excellent fluorescent dye which attracted increasing attention based on easy-dressing,higher fluorescence quantum yields,high molar extinction coefficient,photochemical stability,sharp intense absorption and energy-and electron-transfer capabilities.Moreover,they played an important role in ions detection,molecular probe,cellular imaging,photodynamic therapy and many other fields.It is significant to combine the BODIPY fluorophore with cyanuric chloride to construct the triazine derivatives which have the BODIPY fluorophores.In this case,the rest of two reaction positions on the cyanuric chloride can be used for bridging other functional groups to construct the triazine-BODIPY ring possessing the unique structure.And these novel functional molecules might have special properties,which exhibit good academic significance and potential application prospects.In this paper,by using OH-BODIPY as the raw material and cyanogen chloride as the bridging core,a series of BODIPY derivatives bearing triazine ring were synthesized via step-by-step nucleophilic substitution and their properties were investigated in details.The main contents are as follows:First,the four star-like BODIPY dyes were designed and synthesized.They possess good photophysical properties.The fluorescence properties of the two BODIPY fluorophores dimer 14 are particularly prominent among these derivatives,the BODIPY trimer 15,indicating that the too much BODIPY units might be not favorable for excellent fluorescence due to the possible aggregate-induced quenching.Second,the tripod BODIPY derivatives which bearing two aniline groups 18,20 and 21 were designed and synthesized.Their fluorescence properties increased sequentially.Furthermore,the compound 20,which is unsubstituted at the 3,5 positions of the BODIPY fluorophore,has a high molar extinction coefficient due to the small resistance benefit to the PET mechanism.The derivative 21 exhibited a longer fluorescent wavelength based on the substituents at 3,5 position of BODIPY fluorophore enlarging the conjugated structures.Third,a series of s-triazine BODIPY derivatives bearing triphenylene were designed and synthesized.The tests showed that they have both fluorescent properties and liquid crystal properties.Moreover,the triphenylene-BODIPY derivatives with the long chain showed the better fluorescent properties than others.Finally,a series of cholesterol-containing triazine BODIPY derivatives were designed and synthesized.It was found that their fluorescence properties were not affected by the introduction of liquid crystal groups.The cholesterol-BODIPY system has not only fluorescence properties but also liquid crystalline properties.The length of alkyl chains made great influence on the performance of liquid crystalline properties.